Sodium bis(trimethylsilyl)amide → HCID 123585157, compound

Participants

Reaction Steps

Into a solution of 2-bromo-5-chloropyridin-3-ol (2.6 g) in DMF (50 mL) was added a 1 M solution of NaHMDS in THF (15 mL), after 30 min., (2-(chloromethoxy)ethyl)trimethylsilane (2.496 g) was added. After stifling for 2 hours at rt., The reaction mixture was extracted with ethyl acetate and washed with brine. After drying and removing the solvent, the residue was purified by silica gel chromatography to provide 3.9 g of 2-bromo-5-chloro-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridine. LCMS [M+H]+: 339.8. 1HNMR (400 MHz, CDCl3) ppm: δ 8.01 (d, J=2.2 Hz, 1H), 7.45 (d, J=2.2 Hz, 1H), 5.31 (s, 2H), 3.79 (t, J=8.4 Hz, 2H), 0.92 (t, J=8.4 Hz, 2H), 0.08 (s, 9H).

Provenance & Evidence